


Viva Las Vegas!

by SherriesMyCherryPie



Category: Supernatural
Genre: Cunnilingus, Drunken Shenanigans, Explicit Consent, Explicit Language, Explicit Sexual Content, F/M, Fellatio, Gambling, Las Vegas, Multi, One Shot Collection, Oral Sex, Plot What Plot/Porn Without Plot, Pool Sex, Reader-Insert, Reader-Interactive, Rough Sex, Shameless Smut, Spanking, Team Free Will, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2015-05-01
Updated: 2015-10-11
Packaged: 2018-03-26 13:15:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 3
Words: 13,788
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3852277
Author URL: https://archiveofourown.org/users/SherriesMyCherryPie/pseuds/SherriesMyCherryPie
Summary: <blockquote class="userstuff">
              <p>Imagine Sam and Dean finally letting you and Cas tag along on their annual weekend in Vegas; and you getting more than you bargained for with Team Free Will. Multi-chaptered with each being a different scenario starring your favourite Supernatural hottie. Now complete!</p>
            </blockquote>





	1. Dean

**Author's Note:**

> So I've planned three chapters for this short fic so that you (the reader) can have some shameless smutty fun with either Sam, Dean or Cas (you choose!) Just to disclaim I don't own Supernatural (sadly) and the title for this fic is stolen from the song "Viva Las Vegas" by Elvis Presley.  
> ENJOY!

"Dean, please!" you whined at the elder Winchester, trying to give him your best puppy-dog eyes complete with a pout. You'd been begging Dean and Sam for  _weeks_ to let you go to Vegas with them, seeing as though they went for a hunting break every year. Although it wasn't really Sam who was to blame though for not letting you go; it was Dean who was adamant that you were staying at the bunker.

Dean turned to look at you from where he was packing his duffel bag. He shot an unimpressed look at you.

"(Y/N), I already said no for crying out loud," he growled. "You need to stay here and hold the fort in case anyone calls."

"So I don't get a break too?" you huffed. "This is so not fair. You and Sam get to have a weekend away from all the crap, why can't I?!"

"It's a brother thing," he muttered simply, turning away from you once more. You'd tried to play the angry card, you'd tried to be desperate and you'd tried to flatter your way in. You'd attempted bribery and blackmail and failed miserably. How would you change their minds? It was like Dean's willpower was made of concrete.

Your reverie was interrupted by Sam's arrival; his own duffel bag in tow. You rounded in on him quickly.

"Sam, PLEEEEEASE!" you begged him, your forehead creased with desperation. "Please let me come to Vegas! I'll behave I swear! I swear I will, you won't even know I'm there! I just want a little break too..." you gushed, looking up at him sadly.

Sam sighed and looked over at his brother. Dean shook his head, an incredulous look plastered on his face. 

"Sammy don't let her get to you," he warned his younger brother, clenching his jaw angrily.

Sam's eyebrows knitted together with guilt that they were leaving you behind. Hopefully Sam, on the other hand, wouldn't require as much persuading.

"She's got a point Dean, it's not really fair that we get to go away for a while and she doesn't," Sam reasoned, giving his Dean a stern look.

"Sammy, no-" Dean went to reply.

"What do I have to _do_ God dammit for you to just let me come with you?!" you spat venomously, standing in between them and looking at them each in turn. "You guys can do whatever the hell you normally do, it's like I won't even be there. When we're there I'll mind my own business, I'll do whatever I want and leave you guys to do what you want."

Dean scoffed. "Like that's gonna happen. Remember the last time you went off in a strange place on your own? You became a side order for a Djinn."

You sighed. "Just... Please let me come with you guys. You can sleep with as many chicks as you want, I don't care. I don't care what you do, just let me tag along for the ride." You looked down at the floor before Sam and Dean exchanged glances. 

After a few moments of silence, Dean finally muttered, "fine." Your head shot up and you ran over to him, engulfing him into a giant hug.

"Thankyou thankyou thankyou Dean!" you yelled gleefully, bouncing up and down. You ran over to Sam and repeated your actions. "I promise you guys, you won't regret it! I'm gonna quickly pack some stuff then I'll be ready!"

You made a beeline for the door. "There's just one condition..." Dean said before you could reach it. You turned on your heel to face him, an eyebrow raised questioningly. 

He smirked at you. "Cas is coming too. To... Watch over you like the sweet, innocent Guardian Angel he is."

Your stomach plummeted. Seriously... _A babysitter? At your age?_

* * *

By the time you'd packed your things and jumped into the backseat of the Impala, you were so happy that Sam and Dean had finally given into you that you were actually contemplating that Cas being there too wouldn't be such a bad thing. You were sure he wouldn't mind if you asked him to leave you alone for a short while, and at least you would get your own hotel room. 

"Where are we staying anyway you guys?" you asked, having to project your voice a little over  _"The Boys Are Back In Town"_ which was blaring out of the Impala's speakers.

"The Palazzo," Sam replied, gazing out the window at the scenery rolling past.

You recognized that it was a five star hotel complete with a casino. You smirked. "Sure makes a nice change from all those crappy motels."

Sam chuckled at you, whereas Dean... Well, he was slightly annoyed that you were tagging along. He just concentrated on his driving, tight-lipped with stone cold eyes, listening to his loud rock music. You just shrugged him off. You were going to Vegas baby, at last! And if he didn't like it? Well, screw him. You were convinced that you were going to have a great time without him getting you down.

The journey to Vegas was smooth and not as long and tiring as you anticipated. Once you reached the hotel, Dean had already won an argument against the valet staff ("You are  _not_ touching my Baby, pal!") and soon enough you were parked and ready to go inside.

"Where's Cas then?" you idly muttered out loud to Sam as you dragged your bags off the back seat.

He shrugged at you. "Think he's just gonna use his Angel mojo to bag himself a room."

Thank God you wouldn't have to share with him. Having to hunker down with someone who doesn't sleep when you're hungover and just want to vegetate in bed and remain undisturbed? Not a good combo. 

Once you'd grabbed your bags, you pranced happily up to the hotel entrance, greeting everybody that you passed. You probably didn't fit in well with the upperclass crowd in your jeans and tank top, but that wasn't going to dampen your spirits. You had a plan for later on...

You successfully checked in at the desk, and yours, Sam's and Dean's rooms were on the thirteenth floor. You made your way up there in the elevator, not even bothering to wait for the porters to take your belongings up for you. You were a hunter, you sliced Vampire's heads off for Christ's sakes, you could manage a few bags. 

You gasped audibly when you swiped the room key card across the slot in the door and opened it. The room was just... Incredible. You'd presumed it would be, after all, the whole entrance plaza was gold and white marble. _How much had Dean and Sam paid for these rooms?_

You threw your bags onto the floor and let yourself fall onto the bed. It was the softest bed you'd ever laid on, a four poster with dark mahogany wood. The carpet was creamy colored and the walls a simple white, with some gold detail in places. It took your breath away at how beautiful and  _clean_ it was. That was definitely a first after spending most of your life in grungey motels.

Your phone buzzed in your pocket. It was Sam.

_We're going down to the restaurant to have something to eat in an hour or so, probably hit the casino afterwards.  
You're welcome to join if you want to. Just don't tell Dean I invited you._

You smirked to yourself. It was time for your master plan to take place. You had an hour... And you needed to use that time wisely.

* * *

Within the hour, you'd managed to have a shower, wash your hair, shave your body, brush your teeth, moisturize  _and_ style your hair along with applying some make-up. Normally you wouldn't make this much effort, but this was Vegas, and you counted it as a holiday. 

You slipped on a matching black lacy lingerie ensemble and gazed satisfactorily at the dress that laid on your bed. You'd saved it specifically for special occasions only, and Sam, Dean and Cas had never seen you in it. It was an elegant LBD that was underwired to frame your curves perfectly, and matched with black stilettos, you'd never not scored a hot guy wearing it. 

You pulled it on carefully and grabbed your matching black clutch bag filled with essentials (phone, cash, room key card, demon knife and a small flask of holy water.) You quickly spritzed on a little of your favorite perfume and glanced at your reflection in the mirror. You couldn't help but smile.

You made your way down to the entrance plaza, smirking internally at the looks you were receiving; hungry ones from men, envious ones from women. You tottered along the marble flooring in your heels to the restaurant, informing the attendant at the booking area that you would be seated at the Winchester table. He led you over, and once Sam, Dean and surprisingly Cas were in your vision, you thanked him and made your own way over.

"Good evening gentlemen," you purred proudly as you reached the table. Your stomach somersaulted when all three men turned to look at you, eyes wide and mouths open slightly, even Cas who wasn't particularly subject to human emotion. 

"Hey (Y/N), wow you look great," Sam told you, getting up to give you a hug. You pecked him on the cheek daintily before taking a seat next to him, as the other two men didn't rise to their feet to greet you. 

You glanced over at Dean, who was still staring at you, his gaze almost burning into your skin. You shifted in your seat slightly. Were you really having this effect on the stubborn Dean Winchester? A slight smile tugged at your lips.

You looked over at Cas who flashed you a gentle smile. He'd lost his trench coat for the evening (probably under the advice of Sam and Dean) and was wearing his white shirt, blue and white tie and black dress pants. Dean and Sam too looked very smart for the occasion, wearing their best black suits with white shirts and black ties that they normally wore when posing as FBI. 

"You look very pretty (Y/N)," Cas spoke to you, his puppy-dog eyes looking into yours. You blushed a little. 

"Aw, thanks Cas," you replied. "You look nice too. It's good to see you without that trench coat." You gave a light chuckle, which he reciprocated.

"Thankyou," he murmured softly. He looked down at his lap and back up to you again. "I think I have a... What do humans call it? A "boner"? Hm. I think I have a "boner" now after seeing you in that dress."

Your eyes widened slightly, Sam almost spat out the drink that he was sipping and Dean groaned. "You're not supposed to be open about it," Dean growled to Cas in a low tone. "You're supposed to hide it. Or... Or take care of it or something. Go to the bathroom Cas."

Cas's eyebrows furrowed in sadness as he obviously thought he had done something really wrong to upset Dean. He mumbled his apologies before disappearing into thin air, the light flutter of wings echoing behind him. 

You sighed. "Don't be so hard on him Dean," you chided the elder Winchester. "You know he can't help it. He doesn't know what he's saying, sometimes."

Dean rolled his eyes and gestured for the waiter to come over. "Let's eat. I wanna get to that casino."

* * *

The service you'd received at the restaurant was great; the three course meal came and went within an hour, and two whole bottles of wine had been consumed by the three of you. You felt awful about how Dean was with Cas... You knew that the pair shared a more 'profound bound', but that didn't give Dean the excuse to be a dick to him. You made a mental note to check on him later. That was if you would remember. You were already slightly tipsy due to the wine, and now you were going to drink even more at the casino.

You strolled through the plaza with Dean and Sam to the casino, which was on the ground floor with the restaurant but a small distance away. When you reached it, it was everything you'd ever dreamed of. You'd never actually set foot in a casino, but you'd won a few poker games at The Roadhouse with Ellen, Jo and Ash when they were alive, so you hoped that beginner's luck would be in your favor tonight.

You purchased the drinks at the bar for the three of you and went over to Sam and Dean who were at the roulette table. The atmosphere was so lively and buzzing it was unreal. It was plain to see that even Sam and Dean were starting to enjoy themselves more now.

After  _quite_ a few drinks and games of poker and roulette, you were starting to feel well and truly woozy. The cash you'd all won just went on more booze. You tried not to stumble around in your heels as you switched from table to table and game to game. Sam and Dean had gone off on their own for a while (no doubt to search for some ladies) to leave you to gamble alone and flirt your way into winning cards against random guys. 

It wasn't too much later you were trying to feign off rogue intentions.

"You should come up to my room babe... I'll show you a good time..." a short, forty-something guy who you'd learned was called Alex was slurring at you.

You grimaced a little. "No thanks sweetheart. I'm a little too drunk for that and so are you," you replied, your hunter instincts still quite sharp despite your intoxication.

"Come on... Come and have a few drinks with me..." He draped a flabby arm around your shoulders in an attempt to coerce you. You tried to shrug him off.

"I said  _no thanks,_ " you insisted.

He gripped you a little too tightly for your liking. "Come with me..."

"Do you not know the meaning of the word no?!" You wriggled out of his grasp, but he grabbed your arm again. He was really starting to piss you off now and you didn't want to have to put him down in the middle of the casino.

"Come with me you little bitch," he growled, getting angry now as his fingers pressed into your skin tightly.

"I believe the lady said no, pal," a deep, rough voice echoed. You looked up and saw Dean, standing in front of Alex with an icy glare in his eyes. "Now let her go," he continued through gritted teeth. 

Alex took one look at Dean and huffed, before letting you go, shoving you into the bar and stalking off. You growled to yourself and absent-mindedly rubbed at the arm he'd grabbed.

"Are you okay?" Dean asked, genuine concern dancing in his eyes as he observed you. You nodded.

"Yes. Dean, you do know that I could have taken that guy down," you muttered, turning to the bar and downing a shot of God knows what the bartender had poured you.

"Didn't look like you were going to."

"You didn't give me chance." 

You turned to Dean, who was in a closer proximity to you than he'd ever been before. You could almost feel his body heat radiating from him. "But... Thanks anyway." You smiled wanly. "Where's Sam?"

Dean shrugged. "Think he met a nice lady named Felicia. Sounds a lot like fellatio if you ask me." He flashed a smirk.

You giggled in response at his sense of humor. "Didn't find a lady drunk enough yourself, then?" you teased.

He bit his lip. "I'm still looking, I guess."

"Well good luck with that."

You ordered a martini for yourself and a whiskey for Dean, and the pair of you went to sit outside on the terrace. It was a lovely hot summer's night. It was getting quite late; you wondered idly why Dean had opted to stay with you rather than continuing his sex conquest. Alcohol drowning out your inhibitions and qualms, you decided to ask him.

"You didn't even want me to come on this trip, and now you're choosing to babysit me rather than hook up with somebody?"

To your surprise, Dean didn't take offence. He just chuckled.

"Yeah, well. I guess I knew that  _that_ would happen," he replied, gesturing towards the casino where the incident with Alex had occurred.

"That's why you didn't want me to come?" you continued, looking at him with raised eyebrows.

He took a deep breath, before turning to look you in the eye. "I don't like it when other men talk to you, (Y/N)," he murmured. "I don't even like it when they look at you. And there's a lot of dicks here in Vegas."

You gazed into his mesmerizing green orbs for a few seconds, searching them for some unspoken answers. "Why?" you almost whispered in response.

He looked down at his glass of whiskey, letting the amber liquid slosh around the glass. "Because I want to keep you safe. You're too... Valuable."

You felt shocked. Dean Winchester thought of you as 'valuable?' You could feel your stomach start to flutter. Were you getting  _butterflies_ for Christ's sake?

You just smiled genuinely back at Dean, unsure of what to say. He looked back up at you, his face just inches away from yours, and returned the smile. He chuckled to himself.

"Ah, what the hell. I guess what I'm  _trying_ to say is... I like you, (Y/N). Despite you being very annoying and stubborn sometimes, I really do like you. A lot."

You felt your heart literally leap. "Then why didn't you just say? Instead of acting like a complete douchebag," you replied breathlessly with a slight giggle.

He grinned back at you. "Sorry," he apologized. "Things just seem easier that way sometimes."

You nodded in appreciation to what he said. As much as it irritated you, he had a point; sometimes putting on a facade and pretending was so much easier than dealing with the bigger issues that laid beneath.

"So what's next for you Dean? It's getting late," you noted, sipping at your martini. "Best make a move otherwise all the good ones will have gone." You gestured with your head to the casino.

He crinkled his nose. "Nah, I don't think so."

Your eyes widened in mock horror. "Dean Winchester passing up an opportunity to get laid? Are you feeling okay?"

He laughed under his breath. "Truth is, no female in that room is even half as beautiful as you are, (Y/N)."

You stared at each other for a few brief moments, his gaze flitting from your eyes down to your mouth. You did the same, noticing now how soft and inviting his lips were to you now.

Painfully slowly, the gap between you closed, and your eyes fluttered closed as he pressed his warm mouth to yours. Your stomach flipped excitedly and your clitoris twinged at the thought of where this intervention would lead. He broke away from you after a few seconds, his nose against yours, looking into your eyes like he could see into your soul. You each placed your half empty glasses on the table in front of you and your lips met again, this time more passionately. You moved together in perfect synchronization, his tongue darting over your lower lip seductively, requesting your permission. You opened your mouth to gain him access, and your tongues danced in harmony.

You wrapped your arms round his neck, pulling him closer to you, while his hands snaked round your waist, holding you. You moaned into the kiss at his touch, encouraging him to hold you a little tighter. As the kiss got more heated, you were forced to break away for air. You inhaled and exhaled heavily, catching your breath.

"Shall we go to my room?" you whispered in askance to him. He simply nodded in reply, and you both jumped up from your seats and made your way hurriedly through the now less busy casino.

Once you reached the empty elevator, you could hardly keep your hands off each other again. Your hands roamed his shoulders and chest, grabbing fistfuls of his hair, while he ghosted his way over the curve of your ass, round your waist, up to massage your breasts. Every time the elevator bell sounded you groaned and broke away from each other while other guests entered the elevator, and you had to try to act like you hadn't just been making out. The journey up to the thirteenth floor was painstakingly slow, with guests getting in and out, forcing you to break away and then resume your activities once it was vacant again.

Finally you reached your floor. You pulled Dean along by the hand down the long corridor until you reached your room. You rapidly retrieved the room key card from your clutch and swiped it across the slot, the door opening to grant you access. You led Dean into the room and playfully pushed him onto the bed. He sat up quickly, shrugging off his suit jacket and tossing it on the floor. You pulled the hem of your dress up and lifted it over your head, exposing your sexy lingerie set to Dean, before straddling his lap and kissing him fiercely again.

His hands continued to work their way over your body, lingering over your ass and breasts especially. He broke away from you to pepper kisses along your neck and collarbone, nipping and sucking at the skin there, causing you to moan and grind against his lap. You could feel the huge erection he was sporting through his trousers, causing them to tent slightly.

You worked on removing his tie and unbuttoning his shirt, revealing to you his toned, tanned pectoral and abdominal muscles. You groaned in appreciation at his body and laid him back on the bed so that you could plant a kiss over the anti-possession tattoo he donned on his chest. You made your way down his torso, nuzzling your nose into his abs, until you reached his belt. You unbuckled it quickly and undid his trousers, him breathing heavily beneath you.

You pulled Dean's trousers and boxer shorts down, letting his huge cock spring free from its imprisonment. He gasped and groaned "fuck" under his breath as you took his length in your hand, pumping it slowly. You eagerly wrapped your lips around the head, wanting to taste him. He closed his eyes and threw his head back as you proceeded to take him into your mouth, all the way to the back of your throat. 

"Son of a bitch, (Y/N) that feels amazing," he praised you as he looked down at you sucking his cock. He ran a hand through your hair, pushing you down on him gently.

You moaned as you sucked, the vibrations against his cock sending him wild. You used your free hands to cradle his balls, massaging them carefully as you bobbed up and down, increasing your speed and suction.

Eventually he sat up and pulled you off him so that you could switch places. He kissed you passionately before roughly laying you down on the bed next to him. He worked his way down your body as you had done to him, placing gentle kisses over you torso and grazing his teeth against your skin here and there. You leaned up on your elbows so that he could remove your bra, impressively with one hand, and you gasped and bucked your hips as he took a nipple in your mouth, sucking on it gently. He toyed with the other with his deft fingers, and you moaned his name out loud out loud once more when he bit the hardened bud softly.

He continued his journey, dragging his lips along your stomach, before reaching the waistline of your panties. You whimpered as he nuzzled his nose against your covered pussy, before deciding to tease you by placing chaste kisses along your thighs. 

"Mmm... Dean... Please..." you mewed as he got closer to your most intimate place, where you  _really_ wanted him to be.

He tugged your panties down over your silky thighs, dragging the material down slowly, before resuming his position at the top of your thighs. You felt your clitoris throb at his warm breath so close, and he took you by surprise when you felt his hot, wet tongue probing at your entrance. He licked a broad stripe up your slit to your clitoris, licking gently as you writhed and whimpered helplessly beneath him.

"Uh! Dean!" 

Your moans and growls were becoming more needy. You ground your hips against his tongue in earnest, unable to keep your body still as your core pooled with desire. Dean took your clitoris into his mouth and started to suck gently on it, providing you the leverage you needed. When he finally inserted one of his long fingers inside you, curling it up to stroke your G-spot, that was the final straw. You felt your walls throb endlessly as you neared your climax.

"You're gonna make me come, Dean," you breathed, your chest heaving.

"Come for me baby," Dean replied, giving you the encouragement you needed.

Your walls throbbed for the final time before they released, wrapping around Dean's finger tightly. You all but screamed as you came. You relaxed into the sheets for a few brief moments, coming down from your high, Dean hovering over you and covering your neck with kisses.

"Wow..." you murmured, your eyes closed in sheer bliss. You sighed happily and opened your eyes, face to face with Dean who was grinning happily.

"Enjoyable enough for you?" he asked huskily. You nodded frantically.

He smirked. "Let's see if I can make you come for me again."

Your clitoris twinged again at his statement as he rooted through his jacket pocket for a condom, tearing the foil carefully and rolling it down his shaft. He positioned himself at your entrance.

"Ready sweetheart?"

"Oh yes."

And with that he plunged himself into you, your walls stretching to accommodate him. You cried out in pleasure at being filled to the hilt. "Oh! Dean!"

He grunted as he withdrew his cock from your slick folds before pounding into you again and again, the head of his cock grazing against your sweet spot tantalizingly. You clawed your fingernails down his back and wrapped your legs round his waist as he pumped into you, kissing you and biting your lip roughly, stifling your moans just a little.

"Holy shit," he growled between thrusts. "You're so God damn tight..."

You arched your back off the bed slightly, wanting to feel the full potential of Dean's cock inside you. Both of your moans, groans and profanities echoed throughout the large room for the duration of your love-making session; a light sheen of sweat covered you both as he flipped you over to continue doing you but from behind. The way he spanked your ass and gently pulled on your hair only led to yet another orgasmic build up.

"Are you gonna come for me again sweetheart?" Dean growled as he gripped your hips tightly so that he could slam into you over and over.

"Yes Dean, yes," you whimpered to him as you felt your walls start to tighten and throb for the second time that night. Sensing you start to reach your high, Dean only fucked you faster, spilling you both over the edge as you came around him. The change in climate encouraged Dean's orgasm too, him spilling out his seed inside you shouting your name.

He withdrew his cock for the final time and collapsed onto the pillows, breathing heavily and sweating a little. You crawled up to him and snuggled into his chest, and he wrapped his arms around you and kissed your forehead affectionately.

"That was amazing," he murmured to you. You sighed joyfully again.

"I can safely say the same."

You looked up at him and placed a chaste kiss on his cheek.

"Are you glad I came to Vegas?" you wondered out loud.

He let out a light chuckle. "Fuck yeah."


	2. Sam

**Summary for the Chapter:**

> Imagine Sam and Dean finally letting you and Cas tag along on their annual weekend in Vegas; and you getting more than you bargained for with Team Free Will. Multi-chaptered with each being a different ending scenario starring your favourite Supernatural hottie.

**Notes for the Chapter:**

> So just to make things clear: the first third of the chapter is exactly the same as Dean's (so that readers, if they want to, can just skip to the chapter with the hottie they want to read about without having to read all of the chapters.) All the chapters start off in the same way but lead to a different scenario and a different ending. Just wanted to let you guys know :) Sorry it took so long for me to update I've been so God damn busy so I'm so sorry!   
> Just to disclaim: I don't own Supernatural (sadly) and the title of this fic is stolen from the song "Viva Las Vegas" by Elvis Presley. Enjoy!

"Dean, please!" you whined at the elder Winchester, trying to give him your best puppy-dog eyes complete with a pout. You'd been begging Dean and Sam for weeks to let you go to Vegas with them, seeing as though they went for a hunting break every year. Although it wasn't really Sam who was to blame though for not letting you go; it was Dean who was adamant that you were staying at the bunker.

Dean turned to look at you from where he was packing his duffel bag. He shot an unimpressed look at you.

"(Y/N), I already said no for crying out loud," he growled. "You need to stay here and hold the fort in case anyone calls."

"So I don't get a break too?" you huffed. "This is so not fair. You and Sam get to have a weekend away from all the crap, why can't I?!"

"It's a brother thing," he muttered simply, turning away from you once more. You'd tried to play the angry card, you'd tried to be desperate and you'd tried to flatter your way in. You'd attempted bribery and blackmail and failed miserably. How would you change their minds? It was like Dean's willpower was made of concrete.

Your reverie was interrupted by Sam's arrival; his own duffel bag in tow. You rounded in on him quickly.

"Sam, PLEEEEEASE!" you begged him, your forehead creased with desperation. "Please let me come to Vegas! I'll behave I swear! I swear I will, you won't even know I'm there! I just want a little break too..." you gushed, looking up at him sadly.

Sam sighed and looked over at his brother. Dean shook his head, an incredulous look plastered on his face. 

"Sammy don't let her get to you," he warned his younger brother, clenching his jaw angrily.

Sam's eyebrows knitted together with guilt that they were leaving you behind. Hopefully Sam, on the other hand, wouldn't require as much persuading.

"She's got a point Dean, it's not really fair that we get to go away for a while and she doesn't," Sam reasoned, giving his Dean a stern look.

"Sammy, no-" Dean went to reply.

"What do I have to  _do_  God dammit for you to just let me come with you?!" you spat venomously, standing in between them and looking at them each in turn. "You guys can do whatever the hell you normally do, it's like I won't even be there. When we're there I'll mind my own business, I'll do whatever I want and leave you guys to do what you want."

Dean scoffed. "Like that's gonna happen. Remember the last time you went off in a strange place on your own? You became a side order for a Djinn."

You sighed. "Just... Please let me come with you guys. You can sleep with as many chicks as you want, I don't care. I don't care what you do, just let me tag along for the ride." You looked down at the floor before Sam and Dean exchanged glances. 

After a few moments of silence, Dean finally muttered, "fine." Your head shot up and you ran over to him, engulfing him into a giant hug.

"Thankyou thankyou thankyou Dean!" you yelled gleefully, bouncing up and down. You ran over to Sam and repeated your actions. "I promise you guys, you won't regret it! I'm gonna quickly pack some stuff then I'll be ready!"

You made a beeline for the door. "There's just one condition..." Dean said before you could reach it. You turned on your heel to face him, an eyebrow raised questioningly. 

He smirked at you. "Cas is coming too. To... Watch over you like the sweet, innocent Guardian Angel he is."

Your stomach plummeted. Seriously...  _A babysitter? At your age?_

* * *

By the time you'd packed your things and jumped into the backseat of the Impala, you were so happy that Sam and Dean had finally given into you that you were actually contemplating that Cas being there too wouldn't be such a bad thing. You were sure he wouldn't mind if you asked him to leave you alone for a short while, and at least you would get your own hotel room. 

"Where are we staying anyway you guys?" you asked, having to project your voice a little over  _"The Boys Are Back In Town"_  which was blaring out of the Impala's speakers.

"The Palazzo," Sam replied, gazing out the window at the scenery rolling past.

You recognized that it was a five star hotel complete with a casino. You smirked. "Sure makes a nice change from all those crappy motels."

Sam chuckled at you, whereas Dean... Well, he was slightly annoyed that you were tagging along. He just concentrated on his driving, tight-lipped with stone cold eyes, listening to his loud rock music. You just shrugged him off. You were going to Vegas baby, at last! And if he didn't like it? Well, screw him. You were convinced that you were going to have a great time without him getting you down.

The journey to Vegas was smooth and not as long and tiring as you anticipated. Once you reached the hotel, Dean had already won an argument against the valet staff ("You are  _not_  touching my Baby, pal!") and soon enough you were parked and ready to go inside.

"Where's Cas then?" you idly muttered out loud to Sam as you dragged your bags off the back seat.

He shrugged at you. "Think he's just gonna use his Angel mojo to bag himself a room."

Thank God you wouldn't have to share with him. Having to hunker down with someone who doesn't sleep when you're hungover and just want to vegetate in bed and remain undisturbed? Not a good combo. 

Once you'd grabbed your bags, you pranced happily up to the hotel entrance, greeting everybody that you passed. You probably didn't fit in well with the upperclass crowd in your jeans and tank top, but that wasn't going to dampen your spirits. You had a plan for later on...

You successfully checked in at the desk, and yours, Sam's and Dean's rooms were on the thirteenth floor. You made your way up there in the elevator, not even bothering to wait for the porters to take your belongings up for you. You were a hunter, you sliced Vampire's heads off for Christ's sakes, you could manage a few bags. 

You gasped audibly when you swiped the room key card across the slot in the door and opened it. The room was just... Incredible. You'd presumed it would be, after all, the whole entrance plaza was gold and white marble.  _How much had Dean and Sam paid for these rooms?_

You threw your bags onto the floor and let yourself fall onto the bed. It was the softest bed you'd ever laid on, a four poster with dark mahogany wood. The carpet was creamy colored and the walls a simple white, with some gold detail in places. It took your breath away at how beautiful and clean it was. That was definitely a first after spending most of your life in grungey motels.

Your phone buzzed in your pocket. It was Sam.

 _We're going down to the restaurant to have something to eat in an hour or so, probably hit the casino afterwards._  
_You're welcome to join if you want to. Just don't tell Dean I invited you._

You smirked to yourself. It was time for your master plan to take place. You had an hour... And you needed to use that time wisely.

* * *

 Within the hour, you'd managed to have a shower, wash your hair, shave your body, brush your teeth, moisturize and style your hair along with applying some make-up. Normally you wouldn't make this much effort, but this was Vegas, and you counted it as a holiday. 

You slipped on a matching black lacy lingerie ensemble and gazed satisfactorily at the dress that laid on your bed. You'd saved it specifically for special occasions only, and Sam, Dean and Cas had never seen you in it. It was an elegant LBD that was underwired to frame your curves perfectly, and matched with black stilettos, you'd never not scored a hot guy wearing it. 

You pulled it on carefully and grabbed your matching black clutch bag filled with essentials (phone, cash, room key card, demon knife and a small flask of holy water.) You quickly spritzed on a little of your favorite perfume and glanced at your reflection in the mirror. You couldn't help but smile.

You made your way down to the entrance plaza, smirking internally at the looks you were receiving; hungry ones from men, envious ones from women. You tottered along the marble flooring in your heels to the restaurant, informing the attendant at the booking area that you would be seated at the Winchester table. He led you over, and once Sam, Dean and surprisingly Cas were in your vision, you thanked him and made your own way over.

"Good evening gentlemen," you purred proudly as you reached the table. Your stomach somersaulted when all three men turned to look at you, eyes wide and mouths open slightly, even Cas who wasn't particularly subject to human emotion. 

"Hey (Y/N), wow you look great," Sam told you, getting up to give you a hug. You pecked him on the cheek daintily before taking a seat next to him, as the other two men didn't rise to their feet to greet you. 

You looked over at Cas who flashed you a gentle smile. He'd lost his trench coat for the evening (probably under the advice of Sam and Dean) and was wearing his white shirt, blue and white tie and black dress pants. Dean and Sam too looked very smart for the occasion, wearing their best black suits with white shirts and black ties that they normally wore when posing as FBI. 

"You look very pretty (Y/N)," Cas spoke to you, his puppy-dog eyes looking into yours. You blushed a little. 

"Aw, thanks Cas," you replied. "You look nice too. It's good to see you without that trench coat." You gave a light chuckle, which he reciprocated.

"Thankyou," he murmured softly. He looked down at his lap and back up to you again. "I think I have a... What do humans call it? A "boner"? Hm. I think I have a "boner" now after seeing you in that dress."

Your eyes widened slightly, Sam almost spat out the drink that he was sipping and Dean groaned. "You're not supposed to be open about it," Dean growled to Cas in a low tone. "You're supposed to hide it. Or... Or take care of it or something. Go to the bathroom Cas."

Cas's eyebrows furrowed in sadness as he obviously thought he had done something really wrong to upset Dean. He mumbled his apologies before disappearing into thin air, the light flutter of wings echoing behind him. 

You sighed. "Don't be so hard on him Dean," you chided the elder Winchester. "You know he can't help it. He doesn't know what he's saying, sometimes."

Dean rolled his eyes and gestured for the waiter to come over. "Let's eat. I wanna get to that casino."

* * *

After dinner, you made your way to the casino with Sam and Dean. You noticed that Dean had disappeared immediately, no doubt going off in search of a good poker game or a hot woman, which left you and Sam. You sighed at Dean's actions and turned to Sam with a smirk. 

"Guess it's just us," you said to the younger Winchester.

"Yup I guess so," he laughed in reply. He rubbed the back of his neck absent-mindedly, something that you'd learned he did when he was feeling nervous.

"So shall we get some drinks and see how many losers we can bankrupt tonight?" you asked, feeling a little shy. You didn't want Sam to think that he was stuck with you now that Dean and Cas had left, although you didn't mind at all. You'd always liked hanging out with Sam as he had similar interests and was a lot more compassionate and sensitive than his brother.

Sam nodded at you in reply with a smile, so you both headed to the bar. You opted for something strong for the pair of you, so the bartender poured you some whiskies and brightly colored cocktails. Not your usual tipple, but hey, this was a holiday after all. Probably the only one you would get for a very long time.

You collected your drinks and walked over to a poker table with Sam. You grinned and gestured for him to join you; you'd been told by Bobby that Sam was a very good poker player and you recollected his anecdote about playing poker with a witch who tried to gain the player's years of life, aging them. Apparently both Dean and Bobby had lost 75 years between them but Sam had won them all back.

You took a seat and Sam sat down next to you, joining the game. A short while later, you couldn't help but shake your head in disbelief as the other players eventually left, leaving Sam to humbly scoop up the winnings from the center of the table.

"So Bobby was right," you confirmed with a laugh. "You are pretty good. Nice poker face."

Sam smiled and shrugged modestly. "That's what it's all about," he told you. He counted through the wad of dollar bills in his hand.

"Guess this should buy us at least five more rounds of drinks," he chuckled. You shook your head again before following him to the bar.

"So what's your poison?" he asked, a grin tugging at his lips. Wow, what a change. Sam Winchester actually having fun? You didn't think that you'd live to see the day. 

"Best make it a vodka," you replied with a smirk.

* * *

A short while later, after a lot of alcoholic consumption, you laughed along with Sam in your animated conversation. You'd given up on gambling, and the pair of you sat at the bar drinking and people-watching.

"If you wanna go off and do your own thing, I don't mind," you slurred slightly to him. "I don't want you to think you're stuck with me or anything like that."

Sam shook his head, grinning. "Don't be silly. I'm having a good time."

You smiled to yourself at his reply, sipping at your cocktail daintily. 

"So what shall we do next? What havoc can we wreak on this place?" Sam chuckled in askance at you. 

You thought to yourself for a few moments. "Hmm... Well, we haven't had chance to check out the rest of the hotel yet," you mused. You looked up at Sam. "Shall we take a walk?"

Sam nodded. "Sure, sounds good," he replied. You both downed the remainder of your drinks and got up to wander around the hotel. You walked past the closed restaurant through the plaza and found yourself in a spa area, which was engulfed in darkness.

"Come on let's see what's in here," you said, picking the lock on the door. Luckily there wasn't any security around, so that you could both have a snoop. Sam followed you through the door, and you lead the way down the dark corridor to another door at the end which wasn't locked.

"Oh. My. God," you whispered just loud enough for Sam to hear as you opened the door, and a huge illuminated swimming pool came into your view. The ceiling was dark with small lights like stars spread across it. 

"Wow that looks amazing," Sam murmured as you both entered the room, marveling at its beauty.

You smirked and turned to Sam. "Fancy a swim?"

Sam laughed, thinking you were joking at first. You raised your eyebrows at him questioningly, and it suddenly dawned on him that you were serious.

"I don't have any swimwear," he replied, looking at you incredulously.

"We're adults, aren't we? Come on Sam," you grinned. "You only live once."

Sam shook his head in disbelief at you as you slid out of your dress, leaving you in your black lacy lingerie. Out of your peripheral vision, you noticed that Sam hadn't taken his eyes off you once. You swelled with pride and smiled to yourself, turning away from him to unhook your bra and wriggle out of your panties before taking a running leap into the pool. Thank goodness you were drunk...

Sam laughed and dodged the water that splashed out of the pool before you resurfaced. He took a deep breath. "I can't believe I'm doing this," he muttered as he slipped off his suit jacket and unbuttoned his shirt hurriedly, revealing his tanned and toned body to you. You licked your lips in appreciation; it was plain to see that Sam really looked after himself.

"Come on Sam," you encouraged him. "The water's lovely."

He chuckled at you while he dropped his trousers, leaving him just in his underwear. You turned round to face the other way to give Sam some privacy, just in case he got a little embarrassed. The next thing you knew, there was a huge splash nearby and you were soaked with the rogue water.

You giggled as Sam resurfaced, shaking his wet hair with his eyes closed, like he was in some kind of cologne advert you'd see on TV. He moved his hair out of his eyes, swimming up to you.

"The water  _is_ lovely," he confirmed with a grin. It took you all of your concentration to not stare at his body when he spoke to you,  _especially_  the half of him that was concealed in a blur beneath the surface of the water.

You were abruptly yanked from your daydream by Sam cheekily splashing you with water in your face.

"Hey!" you gasped, spitting out water that had somehow found its way into your mouth. "Sam Winchester, that was very sneaky!"

You growled as you splashed him back, soaking him once again, but he just laughed. "You're gonna have to try harder than that shrimpy," he teased, knowing that the nickname would rile you (credit to Dean, seeing as though the pair towered over you.)

You narrowed your eyes at him, however unable to look convincing as you couldn't keep your smile off your face. "Oh it's on like donkey kong!" you threatened, splashing him once more and pouncing at him, attempting to drag him underwater with you.

But of course Sam was much too tall and much too strong in comparison, and just threw you back way too easily, laughing wildly. You couldn't believe it; not only were you  _skinny-dipping_ with Sam Winchester, but now you were play-fighting... _Naked! In water!_

You felt your stomach somersault as you fought Sam back, trying to push him and pull him while he defended himself against your attacks. Knowing that you wouldn't win this battle, you made an attempt to swim away, but it wasn't long before he caught up with you. 

"I'm gonna get you now..." he teased, pouncing on you and pushing you into the wall of the swimming pool gently so that you were pinned up against it. "You seem to forget that I know your biggest weakness..." he continued ominously. Your heart thudded in your chest, but before you had chance to reply, he commenced tickling you, prodding your sides under the water.

"Ahhhh Sam stop!" you yelled between giggles, trying to wriggle away from him but coming to no avail.

"Shhh we're not supposed to be in here, remember?" Sam replied, unable to keep from laughing himself as he continued to playfully dig his fingers into your ribs.

"Sam please!" you whimpered, trying to keep quiet, your sides aching from laughing. 

Sam stopped his tickling, smirking at you. "I like hearing that..." he murmured, his face in extremely close proximity to yours.

You looked up at him, your chest heaving due to trying to catch your breath. "You like hearing what?" you questioned quietly.

Sam gazed into your eyes, searching them intensely. "I like hearing you beg me..." he spoke in a low, sultry tone.

You felt your nether regions start to tingle at his comment, slightly stunned by his sudden rush of assertiveness and confidence.

"Really? Well maybe I like begging you," you replied with a smirk tugging at the corners of your mouth.

Sam bit his lip seductively, his gaze flitting from your eyes to your lips in anticipation. The both of you remained silent as you stared into the other's eyes, the air between you thick with sexual tension. 

Sam's eyes darkened from their usual light hazel to a dark brown almost black as he moved even closer to you, before finally closing the gap between you; his hands cupped your face and he placed his wet lips, soft and warm, on yours. 

You snaked your arms round his biceps and shoulders, feeling every ripped ridge of muscle as his mouth moved against your lips, his tongue attacking yours with force. His hands ghosted down your arms, disappearing underwater and slipping round your waist, pulling you as close as possible to him. You moaned into the kiss when you could feel his large erection pressing against your leg.

"Oh... Sam..." you moaned as he trailed kisses across your jaw and over your neck. He took you by surprise as his hands moved up to your breasts, massaging them gently and rolling your hard nipples around with his long, deft fingers. Your clitoris throbbed painfully, aching to be touched by him.

"You don't know how long I've wanted to do this..." he growled, nipping gently at your collarbone as he continued to play with your breasts.

Your chest heaved into his hands as your breathing sped up, your lungs craving the oxygen that was already being used to pump the blood to your nether regions. 

"Sam, please..." you begged in a whisper, urging him to touch you in your most intimate place.

He obeyed your request, his hands slowly and tantalizingly moving down your body. You gasped audibly as he started to gently rub your clitoris, teasing your entrance with his fingers.

"You want me to do it like this?" he murmured in askance. He had stopped kissing your neck and had moved his face back up to yours, his dark eyes searching your own.

"Yes," you whimpered, moaning at the friction he was creating with his hands under the water against your sensitive bundle of nerves.

You moaned audibly and closed your eyes in ecstasy as Sam took you by surprise, dipping his fingers inside you teasingly. "Oh shit, Sam..."

Sam only responded by delving into you further, his fingertips grazing against your G-spot, causing your breath to hitch in your throat and your vaginal walls to throb round his long fingers. He nibbled your earlobe and kissed at your jaw as you writhed, arching your back against the wet tiled side of the pool.

"Sam, please..." you mewed, your fingernails clawing at his back, unable to control yourself as you felt the urge to release your building orgasm.

Sam chuckled, his warm breath tickling the sensitive skin behind your ear. "Not yet," he murmured in a low, sultry tone that only made your clitoris twinge more.

You turned your head to look into his eyes once more. "Maybe we should take this upstairs?" he asked, meeting your gaze.

You shook your head in desperation. "Need you now..." you replied breathlessly as he continued to work his fingers inside you slowly.

"Condom?" he spoke skeptically, an eyebrow raised.

You shook your head again. "No need. I'm on the pill."

A smirk tugged at Sam's lips. "Good."

You smiled back at him, before pouting slightly as he withdrew his fingers from you to place his hands on your hips. He lifted you effortlessly in the water, enabling you to wrap your legs round his waist.

"Let's not waste any more time," he murmured as he positioned his erection at your entrance.

"Let's not," you agreed almost pleadingly.

You couldn't help but cry out Sam's name as he thrust into you slowly, achingly, allowing you to adjust to his generous size.

"Shit, Sam..." you moaned as he withdrew, pumping himself into you again and again, filling you to the hilt and even further than that due to the pressure of the water.

"Oh God, (Y/N)," Sam growled, his forehead creased, kneading your buttocks with his hands under the surface, allowing him the leverage to continue fucking you. "You are so tight..."

You could hardly contain your vocals as he plunged into you, the head of his penis grazing against your sweet spot blissfully, and the combined noise of you both echoed off the walls. You dragged your fingernails over the soft flesh of his shoulders, balancing on the fine line between pleasure and pain, as Sam's incredibly large cock penetrated you deeply over and over.

You could barely take it any more; it was taking you all your restraint to hold on to your orgasm as it neared, your walls throbbing in warning around Sam.

"Sam... I'm gonna come," you whispered in warning.

"Come for me, (Y/N)," Sam growled. "I want to see you come."

Sam's words of encouragement were all it took for you to finally release, shouting his name so loud that it bounced off the walls, your heart feeling like it was going to explode, as your walls tightened around his throbbing member.

"Oh, God," Sam grunted as he pushed into you a final time, your orgasm only encouraging his own as he spilled his seed inside you, burying his face in your neck as he did so. 

The both of you remained still, panting for a few seconds, before Sam eventually withdrew from you. 

"Wow... Sorry. Guess it's been a while," he apologised, obviously talking about how long he'd lasted during the intervention.

You giggled. "No worries, Sam. Me too, I guess." 

You looked back into his eyes, now faded back to their usual hazel colour, and smiled. He reciprocated with a grateful expression.

"Guess we should get going before the hotel notices that they'll need to clean to pool," Sam chuckled.

You nodded your head, unable to stifle a laugh.

"Agreed."


	3. Castiel

"Dean, please!" you whined at the elder Winchester, trying to give him your best puppy-dog eyes complete with a pout. You'd been begging Dean and Sam for weeks to let you go to Vegas with them, seeing as though they went for a hunting break every year. Although it wasn't really Sam who was to blame though for not letting you go; it was Dean who was adamant that you were staying at the bunker.

Dean turned to look at you from where he was packing his duffel bag. He shot an unimpressed look at you.

"(Y/N), I already said no for crying out loud," he growled. "You need to stay here and hold the fort in case anyone calls."

"So I don't get a break too?" you huffed. "This is so not fair. You and Sam get to have a weekend away from all the crap, why can't I?!"

"It's a brother thing," he muttered simply, turning away from you once more. You'd tried to play the angry card, you'd tried to be desperate and you'd tried to flatter your way in. You'd attempted bribery and blackmail and failed miserably. How would you change their minds? It was like Dean's willpower was made of concrete.

Your reverie was interrupted by Sam's arrival; his own duffel bag in tow. You rounded in on him quickly.

"Sam, PLEEEEEASE!" you begged him, your forehead creased with desperation. "Please let me come to Vegas! I'll behave I swear! I swear I will, you won't even know I'm there! I just want a little break too..." you gushed, looking up at him sadly.

Sam sighed and looked over at his brother. Dean shook his head, an incredulous look plastered on his face. 

"Sammy don't let her get to you," he warned his younger brother, clenching his jaw angrily.

Sam's eyebrows knitted together with guilt that they were leaving you behind. Hopefully Sam, on the other hand, wouldn't require as much persuading.

"She's got a point Dean, it's not really fair that we get to go away for a while and she doesn't," Sam reasoned, giving his Dean a stern look.

"Sammy, no-" Dean went to reply.

"What do I have to do God dammit for you to just let me come with you?!" you spat venomously, standing in between them and looking at them each in turn. "You guys can do whatever the hell you normally do, it's like I won't even be there. When we're there I'll mind my own business, I'll do whatever I want and leave you guys to do what you want."

Dean scoffed. "Like that's gonna happen. Remember the last time you went off in a strange place on your own? You became a side order for a Djinn."

You sighed. "Just... Please let me come with you guys. You can sleep with as many chicks as you want, I don't care. I don't care what you do, just let me tag along for the ride." You looked down at the floor before Sam and Dean exchanged glances. 

After a few moments of silence, Dean finally muttered, "fine." Your head shot up and you ran over to him, engulfing him into a giant hug.

"Thankyou thankyou thankyou Dean!" you yelled gleefully, bouncing up and down. You ran over to Sam and repeated your actions. "I promise you guys, you won't regret it! I'm gonna quickly pack some stuff then I'll be ready!"

You made a beeline for the door. "There's just one condition..." Dean said before you could reach it. You turned on your heel to face him, an eyebrow raised questioningly. 

He smirked at you. "Cas is coming too. To... Watch over you like the sweet, innocent Guardian Angel he is."

Your stomach plummeted. Seriously... A babysitter? At your age?

* * *

By the time you'd packed your things and jumped into the backseat of the Impala, you were so happy that Sam and Dean had finally given into you that you were actually contemplating that Cas being there too wouldn't be such a bad thing. You were sure he wouldn't mind if you asked him to leave you alone for a short while, and at least you would get your own hotel room. 

"Where are we staying anyway you guys?" you asked, having to project your voice a little over "The Boys Are Back In Town" which was blaring out of the Impala's speakers.

"The Palazzo," Sam replied, gazing out the window at the scenery rolling past.

You recognized that it was a five star hotel complete with a casino. You smirked. "Sure makes a nice change from all those crappy motels."

Sam chuckled at you, whereas Dean... Well, he was slightly annoyed that you were tagging along. He just concentrated on his driving, tight-lipped with stone cold eyes, listening to his loud rock music. You just shrugged him off. You were going to Vegas baby, at last! And if he didn't like it? Well, screw him. You were convinced that you were going to have a great time without him getting you down.

The journey to Vegas was smooth and not as long and tiring as you anticipated. Once you reached the hotel, Dean had already won an argument against the valet staff ("You are not touching my Baby, pal!") and soon enough you were parked and ready to go inside.

"Where's Cas then?" you idly muttered out loud to Sam as you dragged your bags off the back seat.

He shrugged at you. "Think he's just gonna use his Angel mojo to bag himself a room."

Thank God you wouldn't have to share with him. Having to hunker down with someone who doesn't sleep when you're hungover and just want to vegetate in bed and remain undisturbed? Not a good combo. 

Once you'd grabbed your bags, you pranced happily up to the hotel entrance, greeting everybody that you passed. You probably didn't fit in well with the upperclass crowd in your jeans and tank top, but that wasn't going to dampen your spirits. You had a plan for later on...

You successfully checked in at the desk, and yours, Sam's and Dean's rooms were on the thirteenth floor. You made your way up there in the elevator, not even bothering to wait for the porters to take your belongings up for you. You were a hunter, you sliced Vampire's heads off for Christ's sakes, you could manage a few bags. 

You gasped audibly when you swiped the room key card across the slot in the door and opened it. The room was just... Incredible. You'd presumed it would be, after all, the whole entrance plaza was gold and white marble. How much had Dean and Sam paid for these rooms? 

You threw your bags onto the floor and let yourself fall onto the bed. It was the softest bed you'd ever laid on, a four poster with dark mahogany wood. The carpet was creamy colored and the walls a simple white, with some gold detail in places. It took your breath away at how beautiful and clean it was. That was definitely a first after spending most of your life in grungey motels.

Your phone buzzed in your pocket. It was Sam.

We're going down to the restaurant to have something to eat in an hour or so, probably hit the casino afterwards.  
You're welcome to join if you want to. Just don't tell Dean I invited you.

You smirked to yourself. It was time for your master plan to take place. You had an hour... And you needed to use that time wisely.

* * *

Within the hour, you'd managed to have a shower, wash your hair, shave your body, brush your teeth, moisturize and style your hair along with applying some make-up. Normally you wouldn't make this much effort, but this was Vegas, and you counted it as a holiday. 

You slipped on a matching black lacy lingerie ensemble and gazed satisfactorily at the dress that laid on your bed. You'd saved it specifically for special occasions only, and Sam, Dean and Cas had never seen you in it. It was an elegant LBD that was underwired to frame your curves perfectly, and matched with black stilettos, you'd never not scored a hot guy wearing it. 

You pulled it on carefully and grabbed your matching black clutch bag filled with essentials (phone, cash, room key card, demon knife and a small flask of holy water.) You quickly spritzed on a little of your favorite perfume and glanced at your reflection in the mirror. You couldn't help but smile.

You made your way down to the entrance plaza, smirking internally at the looks you were receiving; hungry ones from men, envious ones from women. You tottered along the marble flooring in your heels to the restaurant, informing the attendant at the booking area that you would be seated at the Winchester table. He led you over, and once Sam, Dean and surprisingly Cas were in your vision, you thanked him and made your own way over.

"Good evening gentlemen," you purred proudly as you reached the table. Your stomach somersaulted when all three men turned to look at you, eyes wide and mouths open slightly, even Cas who wasn't particularly subject to human emotion. 

"Hey (Y/N), wow you look great," Sam told you, getting up to give you a hug. You pecked him on the cheek daintily before taking a seat next to him, as the other two men didn't rise to their feet to greet you. 

You glanced over at Dean, who was still staring at you, his gaze almost burning into your skin. You shifted in your seat slightly. Were you really having this effect on the stubborn Dean Winchester? A slight smile tugged at your lips.

You looked over at Cas who flashed you a gentle smile. He'd lost his trench coat for the evening (probably under the advice of Sam and Dean) and was wearing his white shirt, blue and white tie and black dress pants. Dean and Sam too looked very smart for the occasion, wearing their best black suits with white shirts and black ties that they normally wore when posing as FBI. 

"You look very pretty (Y/N)," Cas spoke to you, his puppy-dog eyes looking into yours. You blushed a little. 

"Aw, thanks Cas," you replied. "You look nice too. It's good to see you without that trench coat." You gave a light chuckle, which he reciprocated.

"Thankyou," he murmured softly. He looked down at his lap and back up to you again. "I think I have a... What do humans call it? A "boner"? Hm. I think I have a "boner" now after seeing you in that dress."

Your eyes widened slightly, Sam almost spat out the drink that he was sipping and Dean groaned. "You're not supposed to be open about it," Dean growled to Cas in a low tone. "You're supposed to hide it. Or... Or take care of it or something. Go to the bathroom Cas."

Cas's eyebrows furrowed in sadness as he obviously thought he had done something really wrong to upset Dean. He mumbled his apologies before disappearing into thin air, the light flutter of wings echoing behind him. 

You sighed. "Don't be so hard on him Dean," you chided the elder Winchester. "You know he can't help it. He doesn't know what he's saying, sometimes."

Dean rolled his eyes and gestured for the waiter to come over. "Let's eat. I wanna get to that casino."

* * *

 

You could barely enjoy the beautiful three course meal that came and went at the thought of poor, innocent, bashful Castiel spending the evening alone due to Dean's irrational words.

"You didn't have to be horrible to him, Dean," you chided the elder Winchester with annoyance on your way to the casino. "Everything he says is what he's heard tumble out of your mouth anyway, so don't be such a hypocrite."

Dean simply rolled his eyes at you. "I'm sure he knows I didn't mean it," he replied gruffly, making a beeline for the bar. "Not my fault he's so damn sensitive."

"So what, you're just gonna leave him to spend the rest of the evening, hell even maybe the weekend, alone?"

"He wanted to tag along!" Dean defended himself. "Geez, and you have to wonder why me and Sammy always do the Vegas weekend  _alone."_

You narrowed your eyes and shook your head in disbelief, folding your arms across your chest. "Dean, he's your  _friend."_

"Well if you care so much, why don't  _you_ go babysit the guy?" Dean retorted, his temper flaring slightly. "Like I said, me and Sammy, this is our thing anyway."

"Point taken," you scoffed at the meaning behind Dean's words. "Starting to wish I hadn't bothered begging you to come, well and truly wasted my time, there."

And with that you turned on your heel and stalked off out the casino, leaving Sam slightly dumbfounded and Dean probably relieved. Sam tried to shout after you, but you just ignored him.

You headed through the marble lobby to the elevator, punching the button a little too hard. Thirteen floors up, you were grateful to be back in your room. You idly wondered about Cas, but trying to find him would be like trying to find a needle in a stack of needles; he could be anywhere.

Instead, squeezing your eyes tightly shut, you took a deep breath and prayed, taking a seat at the end of your bed.

"I pray to thee, Castiel... Cas, where are you man?"

You heard the distinct whoosh of wings, and your eyes snapped open to see Cas standing in front of you.

"(Y/N)?" he asked, his forehead creased a little in confusion. "Did you, uh... Need something?"

"Oh Cas, there you are," you sighed in relief. "I just wondered where you were. I'm sorry that Dean was so mean to you, I just wanted to see if you were alright." You offered a small smile of reassurance.

Cas sighed and smiled wanly in return. "Yeah, I'm fine," he started in his thick, gravelly voice. "It was my mistake. I didn't really, er, think... Before I spoke." He shuffled his feet against the cream carpet awkwardly at the thought of the exchange over dinner.

"You don't have to apologise, Cas," you insisted sternly. "It was Dean's fault. He can be so..." 

"Insensitive?" Cas offered, his smile becoming a bit more genuine now.

You nodded with a chuckle. "Indeed."

Cas nodded in agreement with you, swinging his arms by his side. You had learned that this was something he did when he was feeling nervous or awkward.

"So, I have the rest of the evening free now, since I am officially no longer on speaking terms with Dean. What shall we do?" you asked, standing up to face him.

Castiel's eyebrows knitted together. "Why are you not on speaking terms with Dean?"

You rolled your eyes as you remembered your small disagreement with the elder Winchester. "Well, we sorta had an argument. Well, not really an argument, but... Well I made it pretty clear that he had upset me by upsetting you."

The room was quiet for a few moments as Cas processed what you said. "He upset you... By upsetting me?" he asked timidly.

"Well yeah," you replied. "I didn't like the way he spoke to you, I knew that he made you feel uncomfortable. There was no need for the way he acted."

Cas smiled, his bright blue eyes twinkling happily. "Thankyou, (Y/N). For standing up for me."

You winked back. "Anytime."

You took a seat back on the bed, kicking off your heels which were already starting to irritate your poor ankles. "I think I'm just gonna spend the rest of the night up here," you told Cas. You inhaled slowly. "Did you wanna, you know, chill for a while with me? We could watch some TV?" 

Castiel chuckled at your choice of slang. "Erm, sure. We can 'chill' I guess." He smiled and took a seat on the bed next to you, propping himself up against the wall with some pillows, and you did the same. You flicked on the TV and channel surfed for a while, feeling incredibly at ease with the angel sat next to you.

You settled on a horror movie that you hadn't seen before, called _Friday the 13th_ or something like that. You liked to think that you were immune to those sort of movies - more or less, every day of your life as a hunter was Halloween itself anyway.

The movie was around an hour in. You'd curled your legs up, leaning against Cas a little, your heart beat elevated slightly. You'd clearly underestimated your immunity for this movie, as it was making you jump like crazy. 

"Are you okay, (Y/N)?"

Castiel had startled you a little. You nodded meekly in response.

"Yeah, I'm okay," you assured him.

You watched the grisly scene on screen end, another beginning. A guy and a girl, just talking to each other, before engaging in an extremely heated kiss. One thing led to another, and before you knew it you were viewing a full on sex scene.

You tried not to laugh as you watched Cas cock his head repeatedly in a confused manner out of your peripheral vision.

"Are you okay, Cas?" you took your turn to ask him this time.

"Yeah..." he answered, distracted. "Are they really fornicating, or-"

You giggled. "No, Cas. They're just acting."

He raised his eyebrows in surprise. "Oh. It looks very... convincing..."

You grinned, biting your lip. 

"Oh dear, this is not good..."

You looked round at Cas to discover that he was no longer on the bed next to you.

"Cas?" you asked, looking round the room for the angel.

"Yes, um... I won't be a minute."

You continued to scan the room, stopping when you realised that the sound of his voice was coming from the bathroom. "Cas, is everything alright?" you wondered, an eyebrow raised.

"Yes, everything is fine," he confirmed.

You frowned to yourself for a few seconds before the penny finally dropped.  _Oh..._

"Cas it's fine, you don't have to... go to the bathroom. There's no need to hide, it's perfectly natural," you tried to empathise, not wanting him to feel ashamed of his vessel's sensitive reaction.

"I can't come out, it won't go away," Cas replied disdainfully, peeking round the edge of the door at you.

"Don't worry, just... Don't think about it and it'll go away eventually. Come on, you're missing the movie."

"I feel embarrassed."

"You don't have to be embarrassed, this is me. We're friends, remember? I'm not gonna make fun of you." You smiled sympathetically and patted the empty bed next to you where he had been sat.

Castiel sighed deeply and emerged from the bathroom, his tan trenchcoat now buttoned up, when he usually wore it draped by his sides. He reclaimed his seat on the bed, clearing his throat and adjusting his tie a little, his eyes settling on the screen again. He looked over at you bashfully, his gaze meeting the TV once more.

He sighed again around five minutes later, closing his eyes in exasperation. "It still won't go away, (Y/N)."

You looked up at the poor angel. It was obvious his vessel needed some relief; after all this time Cas had been possessing him, he hadn't once done anything of a sexual nature. You oddly felt the same. 

"Well..." you started, a little unsure of what Castiel's reaction would be. "If you needed any, um... assistance, I would be glad to help..." you offered in a low voice.

His eyes snapped open and he turned to look at you, his blue eyes boring into your own. "...What do you mean?" he asked.

"I mean... I could... You know... If you wanted... If not, I totally understand..." you started to ramble. Maybe it wasn't a wise idea. Cas was your friend, and not only that, he was an angel of the fricking Lord. 

Cas gazed into your eyes, searching them. You could only hope that he wasn't reading your mind.  _Oh, to Hell with_   _it,_ you thought, and you slowly closed the narrow gap between you, pressing your soft lips to his gently. He felt so warm, so comfortable, so...  _familiar._

Your lips lingered on his for a few moments, before you broke away to anxiously await a reaction. Cas looked at you, confused for a few seconds, before the gut instinct of his vessel kicked in. Before you knew it, his lips were on yours again, moving softly, his arms snaking round your waist possessively.

You felt heat pool at your core at his touch; you had almost forgotten how it felt to be touched, be kissed, like this.

You opened your mouth into the kiss, your tongue tracing against his lower lip seductively. He allowed you access, only to fight for dominance with his own tongue in response. You ghosted your hands up his arms to wrap your arms around his neck, pressing yourself flush against him.

Castiel responded by lifting you over to him so you were straddling him. Your hands found the way into his hair, tugging on it at the nape of his neck gently. You moaned into the kiss, feeling positively electric as you grew more and more turned on, wanting more from this intervention.

You broke away from the kiss, gasping for air, to pull your dress up over your thighs and eventually over your head, leaving you in your black, lacy lingerie ensemble. You watched Cas' gaze shift from your face down to your body in clear admiration, his eyes scanning over your breasts and naval.

You worked on unbuttoning his trenchcoat slowly, almost tantalizingly, before sliding it down his shoulders. His white shirt and tie followed closely, leaving a half naked Castiel before your very eyes for the first time. You didn't expect a devout man in which the vessel belonged to have a body like that... Toned, with subtle muscle in the right places.

You felt your clitoris twinge at the sight, eager to get the rest of his clothes off. Your lips met his once more, trailing across his cheek down to his jaw, down to his neck. You felt the vibrations of his voice as he moaned against your kisses, as you continued your journey down south. You planted soft, wet kisses across his collarbone, down his chest, which was now heaving due to his heavy breathing. 

You shimmied your body down a little so that you could continue working your way down, feeling the soft, delicious ridges of his abdominal muscles against your tongue. You nuzzled your nose against the little line of hair that commenced on his stomach and made it's way downwards to your destination.

Castiel watched you with uncertainty as you unbuckled his belt and carefully undid the zipper on his pants. You could feel how rock hard he was underneath your touch as you dragged the material down.

"(Y/N)..." Cas started.

"Shhh, it's okay, Cas," you purred. "I'm gonna take care of you," you promised.

Castiel's look of uncertainty passed, and he smiled at you, his breath still slightly laboured. He shifted slightly to allow you to remove his pants and underwear, his erection springing free from imprisonment. You tossed the garments onto the floor, pausing to marvel at his penis. It was quite a bit bigger than you anticipated.

"Is everything okay?" Cas asked, concern dancing in his eyes once more. You smiled reassuringly.

"Yes, everything is perfect."

You lowered your head to lick a broad stripe up the shaft of his cock, it twitching under your touch excitedly.

Castiel's breathing altered once again, speeding up drastically when you took the head into your mouth, bobbing your head down to take his entire length to the back of your throat.

"Oh...Oh my..." Castiel breathed in surprise at the sensation.

You made your way back up, hollowing your cheeks to increase the suction, before taking hold of his cock at the base as you temporarily withdrew him from your mouth. "Does that feel good?" you asked seductively.

Cas nodded enthusiastically. "Yes, it's very... pleasuring."

You smiled before taking him into your mouth again, your tongue dancing in circles around the head while you pumped at the base. You increased your speed, moaning at the sweet yet bitter taste of his precum.

He continued to groan blissfully beneath you, raking his fingers through your hair as you sucked him. You cupped his balls gently with your free hand, massaging them softly as you took his cock to the back of your throat and back up again, gagging slightly at his size against your tonsils.

You stopped after a short while, his cock leaving your mouth with a slight popping sound. "Do you wanna go... further?" you dared to ask. You didn't want to be selfish, but you had needs too; your clitoris was aching, craving intimacy, and you were so wet you thought you would soak the sheets right down to the mattress. Your panties were already clinging to you rather uncomfortably.

You laid down on the bed next to Cas, looking up at him through lustful, heavily-lidded eyes, as your hand trailed down your stomach to your aching sex. He watched you with a burning intensity as you rubbed gently at your clitoris, arching your back and moaning.

"Castiel, please..." you begged breathlessly, wanting him, no, _needing him,_ inside you.

It didn't take long for him to catch on. Just the mere sound of you moaning his name, and he was on top of you, already positioned before your open legs.

"Are you sure?" he asked consciously.

You nodded. "Please..." you breathed.

Castiel lowered his head to kiss you gently as he positioned himself at your entrance, before sheathing his cock inside your tight, wet pussy, filling you to the hilt.

"Oh! Oh Cas," you mewed at the sensation, clawing at the pillow behind your head, while Castiel too groaned in pleasure above you. He took a moment to accommodate himself inside you, before pulling out and pushing in with a slow force, not wanting to hurt you.

"Oh... Faster, Cas... Harder..." you moaned in encouragement as Cas picked up the pace a little, the head of his cock grazing against your sweet spot beautifully. You arched your back and ground your hips against his to feel the full potential of him as he continued to fuck you.

He buried his face in the crook of your neck as he grunted and groaned. "I... I... I feel like..." he started, but you already knew what he was trying to convey.

"It's okay, Cas. Just go with it... Just let it go..." you breathed in encouragement to the angel as you toyed with your clitoris, feeling your own orgasm start to build, like a spring tightly coiling, ready to release.

With a final thrust into you, Castiel spilled his warm seed inside you, moaning your name gently as he did so. It wasn't long before you succumbed to your own release, your vaginal walls tightening around Castiel's throbbing member.

"Wow..." you purred, slightly dazed as you came down from your high. Castiel looked up at you, a slightly dopey smile on his face.

"I always wondered why Dean made such a huge deal out of sex," he spoke, his voice slightly hoarse. "Now I know why."

You giggled as Castiel withdrew himself from you, collapsing on the empty space of bed next to you. He turned to look at you with a warm smile, gazing into your eyes.

"Thankyou, (Y/N). That was most... incredible."

You smiled back, lacing your fingers with his. "Don't mention it, Cas. Happy to help, any time."


End file.
